Characterization of a photoproduct of 7,12-dimethylbenz[a]anthracene and its effects on chick-embryo cells in culture

Abstract

A common impurity of 7,12-dimethylbenz[a]anthracene was more effective than 7,12-dimethylbenz[a]anthracene in inducing morphological alterations, and in causing an increase in glucose uptake, DNA synthesis and cell number in chick-embryo fibroblasts, Gradual morphological transformation follows the increase in DNA synthesis after 2 days when either primary or secondary cultures are treated with 3 .mu.g of the compound/ml. The compound, isolated from 7,12-dimethylbenz[a]anthracene by alumina column chromatography was characterized by TLC, mass spectroscopy, C-H analysis, UV and NMR spectroscopy and thermal decomposition. It was the photo-oxidation product of 7,12-dimethylbenz[a]anthracene, 7,12-epidioxy-7,12-dimethylbenz[a]anthracene. Some of the biological effects observed after treatment of cultures with 7,12-dimethylbenz[a]anthracene may be due in part to the presence of the photo-oxidation product.